CA1166271A - Discoloration prevention of phenolic antioxidants - Google Patents
Discoloration prevention of phenolic antioxidantsInfo
- Publication number
- CA1166271A CA1166271A CA000387922A CA387922A CA1166271A CA 1166271 A CA1166271 A CA 1166271A CA 000387922 A CA000387922 A CA 000387922A CA 387922 A CA387922 A CA 387922A CA 1166271 A CA1166271 A CA 1166271A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- phenolic
- hydroxylamine
- radicals
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002530 phenolic antioxidant Substances 0.000 title claims abstract description 29
- 238000004649 discoloration prevention Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 12
- 150000002923 oximes Chemical class 0.000 claims abstract description 12
- 150000002443 hydroxylamines Chemical class 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 150000001336 alkenes Chemical group 0.000 claims description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 18
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical group CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical group CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 239000003039 volatile agent Substances 0.000 claims description 3
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 229920001971 elastomer Polymers 0.000 abstract description 12
- 239000005060 rubber Substances 0.000 abstract description 12
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 238000006386 neutralization reaction Methods 0.000 abstract description 6
- 238000003860 storage Methods 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000001627 detrimental effect Effects 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 description 20
- 235000006708 antioxidants Nutrition 0.000 description 20
- 230000003078 antioxidant effect Effects 0.000 description 16
- -1 alkyl radicals Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002845 discoloration Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006452 multicomponent reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/88—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US207,111 | 1980-11-17 | ||
| US06/207,111 US4316996A (en) | 1980-11-17 | 1980-11-17 | Discoloration prevention of phenolic antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1166271A true CA1166271A (en) | 1984-04-24 |
Family
ID=22769240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000387922A Expired CA1166271A (en) | 1980-11-17 | 1981-10-14 | Discoloration prevention of phenolic antioxidants |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4316996A (enrdf_load_stackoverflow) |
| EP (1) | EP0052573B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS57111375A (enrdf_load_stackoverflow) |
| BR (1) | BR8107328A (enrdf_load_stackoverflow) |
| CA (1) | CA1166271A (enrdf_load_stackoverflow) |
| DE (1) | DE3163318D1 (enrdf_load_stackoverflow) |
| DK (1) | DK169784B1 (enrdf_load_stackoverflow) |
| MX (1) | MX159420A (enrdf_load_stackoverflow) |
| ZA (1) | ZA817152B (enrdf_load_stackoverflow) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590231A (en) * | 1983-10-11 | 1986-05-20 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| US4703073A (en) * | 1983-10-11 | 1987-10-27 | Ciba-Geigy Corporation | Alkylated N,N-dibenzylhydroxylamines and polyolefin compositions stabilized therewith |
| US4649221A (en) * | 1984-07-23 | 1987-03-10 | Ciba-Geigy Corporation | Polyhydroxylamines |
| US4612393A (en) * | 1985-04-29 | 1986-09-16 | Ciba-Geigy Corporation | Bis(substituted thioalkyl)hydroxylamines and stabilized polyolefin compositions |
| US4668727A (en) * | 1985-11-21 | 1987-05-26 | Ciba-Geigy Corporation | Ester substituted benzylhydroxylamines and stabilized polyolefin compositions |
| US4673700A (en) * | 1985-11-21 | 1987-06-16 | Ciba-Geigy Corporation | Amide substituted benzylhydroxylamines and stabilized polyolefin compositions |
| US4753972A (en) * | 1985-12-16 | 1988-06-28 | Ciba-Geigy Corporation | Substituted aminoxyethyl phosphonates |
| US4666962A (en) * | 1986-04-04 | 1987-05-19 | Ciba-Geigy Corporation | Compositions stabilized with substituted aminoxy-propanoates |
| US4760179A (en) * | 1986-04-04 | 1988-07-26 | Ciba-Geigy Corporation | Substituted aminoxy-propionamides |
| US4929657A (en) * | 1986-04-04 | 1990-05-29 | Ciba-Geigy Corporation | Substituted aminoxy-propionamides |
| US4918189A (en) * | 1986-12-12 | 1990-04-17 | Ciba-Geigy Corporation | Substituted hydroxylamines and compositions stabilized therewith |
| US4749733A (en) * | 1986-12-12 | 1988-06-07 | Ciba-Geigy Corporation | Substituted hydroxylamines and compositions stabilized therewith |
| US4782105A (en) * | 1987-04-10 | 1988-11-01 | Ciba-Geigy Corporation | Long chain N,N,-dialkylhydroxylamines and stabilized compositions |
| US4876300A (en) * | 1987-12-30 | 1989-10-24 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with long chain N,N-dialkylhydroxylamines |
| US5019285A (en) * | 1990-01-26 | 1991-05-28 | Ciba-Geigy Corporation | Thioalkanoic acid substituted N,N-dialkylhydroxylamines and stabilized lubricant compositions |
| US5045583A (en) * | 1990-04-24 | 1991-09-03 | Ciba-Geigy Corporation | O-alkenyl substituted hydroxylamine stabilizers |
| US5266726A (en) * | 1990-10-22 | 1993-11-30 | Ciba-Geigy Corporation | Sterically hindered oxime color improvers for polyolefin processing |
| US5134183A (en) * | 1990-10-22 | 1992-07-28 | Ciba-Geigy Corporation | Sterically hindered oxime color improvers for polyolefin processing |
| US5262538A (en) * | 1991-05-07 | 1993-11-16 | Ciba-Geigy Corporation | Substituted 1-hydroxy-2,6-diaryl-4-acyloxypiperidines or 1-hydroxy-2,6-diaryl-4-acylaminopiperidines and stabilized compositions |
| US5185448A (en) * | 1991-05-07 | 1993-02-09 | Ciba-Geigy Corporation | Substituted 1-oxy-4-acyloxypiperidine and 1-oxy-4-acylaminopiperidine stabilizers |
| US5180829A (en) * | 1991-05-07 | 1993-01-19 | Ciba-Geigy Corporation | Substituted 1-hydroxy-2,6-diaryl-4-acyloxypiperidines or 1-hydroxy-2,6-diaryl-4-acylaminopiperidines and stabilized compositions |
| US5235056A (en) * | 1992-04-22 | 1993-08-10 | Ciba-Geigy Corporation | Substituted 1-hydroxy-2,6-diaryl-4-piperidone ketals and polymer compositions stabilized therewith |
| US5196565A (en) * | 1992-06-26 | 1993-03-23 | Ciba-Geigy Corporation | Extractive purification of phenols |
| US5632748A (en) * | 1993-06-14 | 1997-05-27 | Linvatec Corporation | Endosteal anchoring device for urging a ligament against a bone surface |
| US5844029A (en) * | 1995-09-25 | 1998-12-01 | General Electric Company | Polymer compositions containing hydrocarbon amine oxide and hydrocarbon amine oxide stabilizer compositions |
| US5866718A (en) * | 1997-03-20 | 1999-02-02 | General Electric Company | Synthesis of tertiary amine oxides |
| US5874619A (en) * | 1998-04-07 | 1999-02-23 | Albemarle Corporation | Reducing the coloration of aromatic diamines |
| US6099530A (en) * | 1998-04-09 | 2000-08-08 | Smith & Nephew, Inc. | Soft-tissue intra-tunnel fixation device |
| US6221107B1 (en) | 1998-08-03 | 2001-04-24 | Mark E. Steiner | Ligament fixation device and method |
| DE10250768A1 (de) * | 2002-10-30 | 2004-05-13 | Basf Ag | Mischungen enthaltend phenolische Stabilisatoren |
| JP4996121B2 (ja) * | 2006-03-31 | 2012-08-08 | 株式会社エーピーアイ コーポレーション | 色相が改善された４，４’−ブチリデンビス（６−ｔｅｒｔ−ブチル−３−メチルフェノール）の製造方法 |
| KR102398814B1 (ko) | 2012-07-31 | 2022-05-17 | 가부시키가이샤 아데카 | 잠재성 첨가제 및 상기 첨가제를 함유하는 조성물 |
| RU2635657C2 (ru) * | 2016-01-29 | 2017-11-15 | Закрытое акционерное общество "Научно-исследовательский центр "Резонанс" (ЗАО "НИЦ "Резонанс") | Обнаружитель маневра баллистической ракеты по фиксированной выборке произведений дальности на радиальную скорость |
| CN113980476B (zh) * | 2021-11-09 | 2023-07-18 | 湖北君健新材料股份有限公司 | 一种抗变色剂复合组合物及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3480391A (en) * | 1967-08-24 | 1969-11-25 | Sinclair Research Inc | Hydroxylamine solutions stabilized with an amide oxime and method for their preparation |
| US3683030A (en) * | 1969-07-14 | 1972-08-08 | Universal Oil Prod Co | Alkylation of phenolic or thiophenolic compounds |
| US3946086A (en) * | 1970-10-28 | 1976-03-23 | Felix Borisovich Gershanov | Method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol |
| US4152531A (en) * | 1971-01-18 | 1979-05-01 | The Goodyear Tire & Rubber Company | Process of preparing phenolic compositions |
| US3746654A (en) * | 1971-02-02 | 1973-07-17 | Goodyear Tire & Rubber | Process for improving the color characteristics of antioxidants |
| US3989665A (en) * | 1975-01-20 | 1976-11-02 | The Goodyear Tire & Rubber Company | Butylated, α-methyl styrenated phenolic antioxidants for polymers |
-
1980
- 1980-11-17 US US06/207,111 patent/US4316996A/en not_active Expired - Lifetime
-
1981
- 1981-10-14 CA CA000387922A patent/CA1166271A/en not_active Expired
- 1981-10-15 ZA ZA817152A patent/ZA817152B/xx unknown
- 1981-10-28 DE DE8181630070T patent/DE3163318D1/de not_active Expired
- 1981-10-28 EP EP81630070A patent/EP0052573B1/en not_active Expired
- 1981-11-11 MX MX190075A patent/MX159420A/es unknown
- 1981-11-12 BR BR8107328A patent/BR8107328A/pt not_active IP Right Cessation
- 1981-11-16 DK DK507081A patent/DK169784B1/da active
- 1981-11-17 JP JP56184345A patent/JPS57111375A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| MX159420A (es) | 1989-05-30 |
| DK169784B1 (da) | 1995-02-27 |
| EP0052573B1 (en) | 1984-04-25 |
| JPH0227388B2 (enrdf_load_stackoverflow) | 1990-06-15 |
| DK507081A (da) | 1982-05-18 |
| ZA817152B (en) | 1982-09-29 |
| EP0052573A1 (en) | 1982-05-26 |
| US4316996A (en) | 1982-02-23 |
| JPS57111375A (en) | 1982-07-10 |
| DE3163318D1 (en) | 1984-05-30 |
| BR8107328A (pt) | 1982-08-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1166271A (en) | Discoloration prevention of phenolic antioxidants | |
| US4446264A (en) | Synergistic antioxidant mixtures | |
| US4439570A (en) | Phenolic antioxidant compositions for organic polymers | |
| US3903049A (en) | Oxidation resistant sulfur curable rubbery polymers | |
| US2801980A (en) | Antioxidant for rubber | |
| US3004035A (en) | Dialkylphenol condensation products | |
| US2964498A (en) | Polythene and polypropylene stabilized with a bis [ortho (1, 1, 3, 3-tetramethylbutyl) phenol] sulphide | |
| US2625568A (en) | Ketone condensation products of bisphenyl type compounds | |
| US2716096A (en) | Stabilized organic compositions containing a ketone condensation product of bisphenyl type compounds | |
| US3935281A (en) | Phenolic antioxidants prepared from a pentacyclo-tetradeca-5,11-diene | |
| US3554964A (en) | Stabilization systems for polymers | |
| CA1323718C (en) | Methylene bis(alkylsulfides) as antioxidant synergists in rubber | |
| US3406158A (en) | Process for the production of sulfurized phenols | |
| US2616871A (en) | Rubber preserved with thiazylthio dihydroxybenzenes | |
| US3209001A (en) | Morpholinothio tert-butyl phenol compounds | |
| US3024217A (en) | Rubber antioxidant | |
| US2690435A (en) | Protection of rubber by stannous complex | |
| US4152531A (en) | Process of preparing phenolic compositions | |
| US2782181A (en) | Oxidizable rubber containing a phthalidyl phenol as antioxidant | |
| US2810731A (en) | Phthalidyl alkyl phenols | |
| US4599464A (en) | Novel compositions | |
| US3502615A (en) | Synergistic antiozonant mixture and use thereof in rubber | |
| US3154517A (en) | Method of vulcanizing rubber in the presence of 2-(2, 6-dimethyl-4-morpholinylmercapto) benzothiazoles and product obtained | |
| US3226359A (en) | Hydrochlorination of polyisoprene in presence of phenols | |
| US3317459A (en) | Rubbers stabilized with the reaction product of halo olefins and phenols |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |